Liquid crystal composition containing polymerizable compound and liquid crystal display element using the same

ABSTRACT

Provided are a liquid crystal composition containing, as a first component, a polymerizable compound represented by general formula (I): 
       (Z 11 ) m11 -M 11 -(L 11 -M 12 ) n11 -COO-(M 13 -L 12 ) n12 -M 14 -(Z 12 ) m12    (I)
 
     and a liquid crystal display element using the liquid crystal composition.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application claims priority under 35 U.S.C. §119 to JapanesePatent Application No. 2010-094922, filed Apr. 16, 2010, which isincorporated herein by reference.

FIELD OF THE INVENTION

The present invention relates to a liquid crystal composition containinga polymerizable compound and a liquid crystal display element using theliquid crystal composition.

BACKGROUND OF THE INVENTION

Polymer sustained alignment (PSA) liquid crystal display elements have astructure in which a polymer structure is formed in a cell in order tocontrol the pretilt angle of liquid crystal molecules, and are expectedto become next-generation liquid crystal display elements because oftheir high-speed responsiveness and high contrast.

Such a PSA liquid crystal display element is produced by injecting apolymerizable composition containing a liquid crystal compound and apolymerizable compound between substrates, and polymerizing thepolymerizable compound while aligning liquid crystal molecules byapplying a voltage, thus fixing the alignment of the liquid crystalmolecules. It is known that the causes of image sticking, which isdisplay damage of this PSA liquid crystal display element, includeimpurities and a change in the alignment of liquid crystal molecules(i.e., change in the pretilt angle).

Image sticking due to impurities is caused by a polymerizable compoundthat remains because of incomplete polymerization and a polymerizationinitiator added for the purpose of accelerating the progress of thepolymerization. Therefore, it is necessary to minimize the amount ofpolymerizable compound remaining after the polymerization and tosuppress the amount of polymerization initiator added. For example, whena large amount of polymerization initiator is added in order tocompletely carry out the polymerization, a voltage-holding ratio of theresulting display element is decreased by the residual polymerizationinitiator, resulting in an adverse effect on the display quality. On theother hand, when the amount of polymerization initiator used in thepolymerization is reduced in order to suppress the decrease in thevoltage-holding ratio, the polymerizable compound remains because thepolymerization does not completely proceed, and thus image sticking dueto the residual polymerizable compound inevitably occurs. In order tosuppress the amount of residual polymerizable compound by completelycuring (i.e., hardening) a polymerizable compound with a small amount ofpolymerization initiator added, a method of applying a large amount ofenergy may be employed, specifically, for example, strong ultravioletlight may be applied for a long time during the polymerization. In thiscase, however, in addition to an increase in the size of a productionapparatus and a decrease in the production efficiency, for example,degradation of a liquid crystal material due to ultraviolet light may becaused. Thus, in existing liquid crystal compositions containing apolymerizable compound, it is difficult to reduce both the amount ofresidual uncured polymerizable compound and the amount of residualpolymerization initiator at the same time. Accordingly, it has beendesired to develop a liquid crystal composition containing apolymerizable compound that is completely polymerized without using apolymerization initiator.

Meanwhile, it is also known that image sticking may be caused by achange in the pretilt angle of liquid crystal molecules in a liquidcrystal composition containing a polymerizable compound. Specifically,in the case where a polymer obtained by curing a polymerizable compoundis flexible, when a display element is fabricated and a certain patternis continued to be displayed for a long time, the structure of thepolymer changes, resulting in the change in the pretilt angle. Sincesuch a change in the pretilt angle may become a cause of image sticking,it is necessary to use a polymerizable compound capable of forming apolymer which has a rigid structure and whose structure does not change.

Hitherto, in order to prevent image sticking by improving the rigidityof a polymer, a display element has been constituted by using apolymerizable compound having a structure such as a 1,4-phenylene grouphaving only a ring structure and polymerizable functional groups (referto Japanese Unexamined Patent Application Publication No. 2003-307720)and a display element has been constituted by using a polymerizablecompound having a biaryl structure (refer to Japanese Unexamined PatentApplication Publication No. 2008-116931). However, these polymerizablecompounds have low compatibility with liquid crystal compounds, and thusdeposition of the polymerizable compounds occurs when a liquid crystalcomposition is prepared. Thus, it is difficult to apply thesepolymerizable compounds to a liquid crystal composition suitable forpractical use.

In addition, in order to prevent image sticking by improving therigidity of a polymer, it has been proposed that a display element isconstituted by using a mixed liquid crystal composition containing abifunctional polymerizable compound and a trifunctional or higherfunctional polymerizable compound such as dipentaerythritolpentaacrylate or dipentaerythritol hexaacrylate (refer to JapaneseUnexamined Patent Application Publication No. 2004-302096). However,since dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylatehave no ring structure in their molecules, the affinity of thesepolymerizable compounds with liquid crystal compounds is weak and aforce that controls the alignment is also weak. Accordingly, sufficientalignment stability is not achieved. Furthermore, it is essential to adda polymerization initiator in polymerization of these polymerizablecompounds. Unless a polymerization initiator is added, thesepolymerizable compounds remain after the polymerization.

As described above, it is difficult to satisfy characteristics desiredin polymerizable-compound-containing liquid crystal compositions, suchas image sticking characteristics of a display element, alignmentstability, stability of the composition having such a property that nodeposition is produced, and the production efficiency in the fabricationof a PSA liquid crystal display element, and this difficulty inhibitspractical application of this display element.

SUMMARY OF THE INVENTION

Accordingly, it is an object of the present invention to provide apolymerizable-compound-containing liquid crystal composition that has astrong force that controls the liquid crystal alignment afterpolymerization and that does not cause a problem such as image sticking.It is another object of the present invention to provide apolymerizable-compound-containing liquid crystal composition in which apolymerizable compound is satisfactorily compatible with liquid crystalmaterials and a problem such as deposition does not occur. Furthermore,it is another object of the present invention to provide a liquidcrystal display element to which a liquid crystal alignment capabilityis provided by polymerization of a polymerizable-compound-containingliquid crystal composition, the liquid crystal display element having agood display performance.

As a result of intensive studies on various polymerizable compounds andvarious non-polymerizable liquid crystal compounds, the inventors of thepresent invention found that a polymerizable-compound-containing liquidcrystal composition containing a polymerizable compound andnon-polymerizable liquid crystal compounds, all of which have specificstructures can achieve the above objects, and this finding led to therealization of the present invention.

The present invention provides a polymerizable-compound-containingliquid crystal composition described below and a liquid crystal displayelement using the liquid crystal composition.

Specifically, the polymerizable-compound-containing liquid crystalcomposition contains,

as a first component, at least one polymerizable compound represented bygeneral formula (I):

(Z¹¹)_(m11)-M¹¹-(L¹¹-M¹²)_(n11)-COO-(M¹³-L¹²)_(n12)-M¹⁴-(Z¹²)_(m12)  (I)

(wherein Z¹¹ and Z¹² each independently represent a hydrogen atom, afluorine atom, a chlorine atom, a cyano group, a thiocyanate group, atrifluoromethoxy group, a trifluoromethyl group, a difluoromethoxygroup, or an alkyl group having 1 to 12 carbon atoms where a methylenegroup in the alkyl group may be substituted with an oxygen atom, asulfur atom, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, or —C≡C— as long asoxygen atoms are not directly bonded to each other, or Z¹¹ and Z¹² eachindependently represent -L¹³-S¹¹—R¹¹ (where L¹³s each independentlyrepresent a single bond, —O—, —S—, —CH₂—, —OCH₂—, —CH₂O—, —CO—, —C₂H₄—,—COO—, —OCO—, —OCOOCH₂—, —CH₂OCOO—, —CO—NR^(a)—, —NR^(a)—CO—, —SCH₂—,—CH₂S—, —CH═CR^(a)—COO—, —CH═CR^(a)—OCO—, —COO—CR^(a)═CH—,—OCO—CR^(a)═CH—, —COO—CR^(a)═CH—COO—, —COO—CR^(a)═CH—OCO—,—OCO—CR^(a)═CH—COO—, —OCO—CR^(a)═CH—OCO—, —COOC₂H₄—, —OCOC₂H₄—,—C₂H₄OCO—, —C₂H₄COO—, —CH₂COO—, —CH₂OCO—, —COOCH₂—, —OCOCH₂—, —CH═CH—,—CF═CF—, —CF═CH—, —CH═CF—, —CF₂—, —CF₂O—, —OCF₂—, —CF₂CH₂—, —CH₂CF₂—,—CF₂CF₂—, or —C≡C— (where R^(a)s each independently represent a hydrogenatom or an alkyl group having 1 to 4 carbon atoms),

-   S¹¹s each independently represent an alkylene group having 1 to 12    carbon atoms or a single bond, where a methylene group in the    alkylene group may be substituted with —O—, —COO—, —OCO—, or —OCOO—    as long as oxygen atoms are not directly bonded to each other,-   R¹¹s each independently represent any one of formulae (R-1) to    (R-15):

however, at least one of Z¹¹ and Z¹² represents -L¹³-S¹¹—R¹¹, M¹¹ andM¹⁴ each independently represent a 1,4-phenylene group, abenzene-1,3,5-triyl group, a benzene-1,3,4-triyl group, abenzene-1,3,4,5-tetrayl group, a 1,4-cyclohexylene group, acyclohexane-1,3,5-triyl group, a cyclohexane-1,3,4-triyl group, acyclohexane-1,3,4,5-tetrayl group, a pyridine-2,5-diyl group, apyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, anaphthalene-2,5,6-triyl group, a naphthalene-2,5,6,7-tetrayl group, a1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a1,2,3,4-tetrahydronaphthalene-2,5,6-triyl group, a1,2,3,4-tetrahydronaphthalene-2,5,6,7-tetrayl group, or a1,3-dioxane-2,5-diyl group, M¹¹ and M¹⁴ may each be independentlyunsubstituted or substituted with an alkyl group having 1 to 12 carbonatoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxygroup having 1 to 12 carbon atoms, a halogenated alkoxy group having 1to 12 carbon atoms, a halogen, a cyano group, or a nitro group,

-   L¹¹ and L¹² each independently represent the same group as that    represented by L¹³,-   M¹² and M¹³ each independently represent a 1,4-phenylene group, a    1,4-Cyclohexylene group, a pyridine-2,5-diyl group,    pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, an    indane-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl    group, or a 1,3-dioxane-2,5-diyl group, M¹² and M¹³ may each be    independently unsubstituted or substituted with an alkyl group    having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to    12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a    halogenated alkoxy group having 1 to 12 carbon atoms, a halogen, a    cyano group, or a nitro group,-   m11 and m12 each independently represent 1, 2, or 3, and when-   m11 and/or m12 represents 2 or 3, Z¹¹s and/or Z¹²s, the number of    which is 2 or 3, may be the same or different, and-   n11 and n12 each independently represent 0, 1, or 2, but n11+n12 is    2 or less, and when nil or n12 represents 2, M¹²s or M¹³s, the    number of which is 2, may be the same or different and L¹¹s or    L12_(s), the number of which is 2, may be the same or different);

as a second component, at least one compound represented by generalformula (II):

R²¹-M²¹-L²¹-M²²-(L²²-M²³)_(o)-R²²   (II)

(wherein R²¹ and R²² each independently represent an alkyl group having1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms,one methylene group or two or more non-adjacent methylene groups in thealkyl group or the alkenyl group may each be substituted with —O— or—S—, and one or more hydrogen atoms in the alkyl group or the alkenylgroup may each be substituted with a fluorine atom or a chlorine atom,

-   M²¹, M²², and M²³ each independently represent a group selected from    the groups consisting of-   (a) a trans-1,4-cyclohexylene group (where one methylene group or    two or more non-adjacent methylene groups in the    trans-1,4-cyclohexylene group may each be substituted with —O— or    —S—),-   (b) a 1,4-phenylene group (where one —CH═ or two or more    non-adjacent —CH═ in the 1,4-phenylene group may each be substituted    with a nitrogen atom), a 2-fluoro-1,4-phenylene group, a    3-fluoro-1,4-phenylene group, and a 3,5-difluoro-1,4-phenylene    group, and-   (c) a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]-octylene    group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a    decahydronaphthalene-2,6-diyl group, and a    1,2,3,4-tetrahydronaphthalene-2,6-diyl group, o represents 0, 1, or    2,-   L²¹ and L²² each independently represent a single bond, —CH₂CH₂—,    —(CH₂)₄—, —OCH₂—, CH₂O—, —OCF₂—, CF₂O—, —CH═CH—, —CH═N—N═CH—, or    —C≡C—, when a plurality of L²²s are present, L²²s may be the same or    different, and when a plurality of M²³s are present, M²³s may be the    same or different) ; and

as a third component, at least one compound selected from the groupconsisting of compounds represented by general formulae (IIIa), (IIIb),and (IIIc):

(wherein R³¹, R³², and R³³ each independently represent an alkyl grouphaving 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbonatoms, one methylene group or two or more non-adjacent methylene groupsin the alkyl group or the alkenyl group may each be substituted with —O—or —S—, and one or more hydrogen atoms in the alkyl group or the alkenylgroup may each be substituted with a fluorine atom or a chlorine atom,M³¹, M³², M³³, M³⁴, M³⁵, M³⁶, M³⁷, and M³⁸ each independently representa group selected from the groups consisting of

-   (d) a trans-1,4-cyclohexylene group (where one methylene group or    two or more non-adjacent methylene groups in the    trans-1,4-cyclohexylene group may each be substituted with —O— or    —S—),-   (e) a 1,4-phenylene group (where one —CH═ or two or more    non-adjacent —CH═ in the 1,4-phenylene group may each be substituted    with —N═), a 3-fluoro-1,4-phenylene group, and a    3,5-difluoro-1,4-phenylene group, and-   (f) a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]-octylene    group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a    1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a    decahydronaphthalene-2,6-diyl group, a hydrogen atom contained in    any of the groups (d), (e), and (f) may be substituted with a cyano    group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy    group, or a chlorine atom,-   L³¹, L³², L³³, L³⁴, L³⁵, L³⁶, L³⁷, and L³⁸ each independently    represent a single bond, —COO—, —OCO—, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—,    —CH₂O—, —OCF₂—, —CF₂O—, or —C≡C—, when a plurality of M³²s, M³⁴s,    M³⁵s, M³⁷s, M³⁸s, L³¹s, L³³s, L³⁵s, L³⁶s, and/or L³⁸s are present,    they may be the same or different,-   X³¹, X³², X³³, X³⁴, X³⁵, X³⁸, and X³⁷ each independently represent a    hydrogen atom or a fluorine atom,-   Y³¹, Y³², and Y³³ each independently represent a fluorine atom, a    chlorine atom, a cyano group, a thiocyanate group, a    trifluoromethoxy group, a trifluoromethyl group, a    2,2,2-trifluoroethyl group, or a difluoromethoxy group, and p, q, r,    s, and t each independently represent 0, 1, or 2, but q+r and s+t    are each 2 or less),-   or at least one compound selected from the group consisting of    compounds represented by general formulae (IVa), (IVb), and (IVc):

(wherein R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, and R⁴⁶ each independently representan alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2to 10 carbon atoms, one methylene group or two or more non-adjacentmethylene groups in the alkyl group or the alkenyl group may each besubstituted with —O— or —S—, and one or more hydrogen atoms in the alkylgroup or the alkenyl group may each be substituted with a fluorine atomor a chlorine atom,

-   M⁴¹, M⁴², M⁴³, M⁴⁴, M⁴⁵, M⁴⁶, M⁴⁷, M⁴⁸, and M⁴⁹ each independently    represent a group selected from the groups consisting of-   (g) a trans-1,4-cyclohexylene group (where one methylene group or    two or more non-adjacent methylene groups in the    trans-1,4-cyclohexylene group may each be substituted with —O— or    —S—),-   (h) a 1,4-phenylene group (where one —CH═ or two or more    non-adjacent —CH═ in the 1,4-phenylene group may each be substituted    with a nitrogen atom), and-   (i) a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]-octylene    group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a    1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a    decahydronaphthalene-2,6-diyl group, a hydrogen atom contained in    any of the groups (g), (h), and (i) may be substituted with a cyano    group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy    group, or a chlorine atom,-   L⁴¹, L⁴², L⁴³, L⁴⁴, L⁴⁵, L⁴⁶, L⁴⁷, L⁴⁸, and L⁴⁹ each independently    represent a single bond, —COO—, —OCO—, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—,    —CH₂O—, —OCF₂—, —CF₂O—, or —C≡C—, when a plurality of M⁴²s, M⁴³s,    M⁴⁵s, M⁴⁶s, M⁴⁸s, M⁴⁹s, L⁴¹s, L⁴³s, L⁴⁴s, L⁴⁶s, L⁴⁷s and/or L⁴⁹s are    present, they may be the same or different,-   X⁴¹, X⁴², X⁴³, X⁴⁴, X⁴⁵, X⁴⁶, X⁴⁷ and X⁴⁸ each independently    represent a hydrogen atom, a trifluoromethyl group, a    trifluoromethoxy group, or a fluorine atom, however, at least one of    X⁴¹ and X⁴² represents a fluorine atom, at least one of X⁴³, X⁴⁴,    and X⁴⁵ represents a fluorine atom, at least one of X⁴⁶, X⁴⁷, and    X⁴⁸ represents a fluorine atom, X⁴⁶ and X⁴⁷ do not represent    fluorine atoms at the same time, and X⁴⁶ and X⁴⁸ do not represent    fluorine atoms at the same time,-   G represents a methylene group or —O—, and-   u, v, w, x, y, and z each independently represent 0, 1, or 2, but    u+v, w+x, and y+z are each 2 or less).

Since the polymerizable compound which is an essential component of thepresent invention has a good compatibility with other non-polymerizableliquid crystal compounds, a stable liquid crystal composition can beobtained. In addition, the polymerizable compound has a skeleton similarto that of a liquid crystal compound, and thus has a strong force thatcontrols the alignment of the liquid crystal compound. Furthermore,according to the liquid crystal composition containing the polymerizablecompound, the polymerizable compound can be polymerized without using aphotoinitiator or by adding a very small amount of a photoinitiator, andan unpolymerized polymerizable compound does not remain afterpolymerization or the amount of such an unpolymerized polymerizablecompound is very small. In addition, energy necessary for thepolymerization of the polymerizable compound can be significantlyreduced. Consequently, it is possible to markedly reduce display damageof a liquid crystal display element to which a liquid crystal alignmentcapability is provided by polymerizing a polymerizable compound in aliquid crystal material. It is also possible to reduce the energy costfor the production and to improve the production efficiency. Thus, theliquid crystal composition containing the polymerizable compound isuseful as a liquid crystal material for the liquid crystal displayelement.

DETAILED DESCRIPTION OF THE PRESENT INVENTION

A polymerizable compound used as a first component in apolymerizable-compound-containing liquid crystal composition accordingto the present invention is a compound represented by general formula(I). In general formula (I), Z¹¹ and Z¹² are each preferably a hydrogenatom, a fluorine atom, a chlorine atom, a cyano group, a thiocyanategroup, a trifluoromethoxy group, a trifluoromethyl group, adifluoromethoxy group, an alkyl group having 1 to 12 carbon atoms wherea methylene group in the alkyl group may be substituted with an oxygenatom, a sulfur atom, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, or —C≡C— aslong as oxygen atoms are not directly bonded to each other, or-L¹³-S¹¹—R¹¹. More preferably, Z¹¹ and Z¹² are each a hydrogen atom, afluorine atom, an alkyl group having 1 to 12 carbon atoms where amethylene group in the alkyl group may be substituted with an oxygenatom, a sulfur atom, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, or —C≡C— aslong as oxygen atoms are not directly bonded to each other, or-L¹³-S¹¹—R¹¹. Still more preferably, Z¹¹ and Z¹² are each a hydrogenatom, an alkyl group having 1 to 12 carbon atoms where a methylene groupin the alkyl group may be substituted with an oxygen atom as long asoxygen atoms are not directly bonded to each other, or -L¹³-S¹¹—R¹¹.

m11 and m12 are each preferably 1, 2, or 3, and more preferably 1 or 2.When m11 and/or m12 represents 2 or 3, Z¹¹s and/or Z¹²s, the number ofwhich is 2 or 3, maybe the same or different. The numbers of Z¹¹s andZ¹²s change depending on the values of m11 and m12, respectively. Inparticular, the number of polymerizable functional groups represented byL¹³-S¹¹—R¹¹ contained in the molecule is important from the standpointof determining the strength of a cured product after polymerization.With the increase in the number of polymerizable functional groups, thestrength of the cured product after polymerization increases.Accordingly, in order to improve the strength, the number ofpolymerizable functional groups is preferably 2 to 6. In order toimprove the compatibility with liquid crystal materials, the number ofpolymerizable functional groups is preferably 1 to 4. From thestandpoint of the balance of these, the number of polymerizablefunctional groups is preferably 1 to 4, and more preferably 1 to 3.

R¹¹ represents a polymerizable group. Specific examples of thepolymerizable group include structures shown below.

These polymerizable groups are cured by radical polymerization, radicaladdition polymerization, cationic polymerization, and anionicpolymerization. In particular, when ultraviolet polymerization isconducted as a polymerization method, the polymerizable grouprepresented by formula (R-1), formula (R-2), formula (R-4), formula(R-5), formula (R-7), formula (R-11), formula (R-13), or formula (R-15)is preferable, the polymerizable group represented by formula (R-1),formula (R-2), formula (R-7), formula (R-11), or formula (R-13) is morepreferable, and the polymerizable group represented by formula (R-1) orformula (R-2) is still more preferable. When a plurality of R¹¹s arepresent in the molecule, they may be the same or different.

S¹¹ represents a spacer group or a single bond. The spacer group ispreferably a single bond or an alkylene group having 1 to 12 carbonatoms, where a methylene group in the alkylene group may be substitutedwith an oxygen atom, —COO—, —OCO—, or —OCOO— as long as oxygen atoms arenot directly bonded to each other. In order to reduce the amount ofchange in the pretilt angle, S¹¹ is preferably a single bond or analkylene group having a carbon chain length of 1 to 4, where a methylenegroup in the alkylene group may be substituted with an oxygen atom,—COO—, —OCO—, or —OCOO— as long as oxygen atoms are not directly bondedto each other. In contrast, in order to improve the solubility, S¹¹ ispreferably a methylene group having a certain degree of length. However,if the length of the methylene group is too long, flexibility of theresulting polymer after polymerization increases, which may become acause of image sticking. For this reason, in order to improve thesolubility, S¹¹ is preferably an alkylene group having 1 to 8 carbonatoms, and more preferably an alkylene group having 1 to 5 carbon atoms,where a methylene group in the alkylene group may be substituted with anoxygen atom, —COO—, —OCO—, or —OCOO— as long as oxygen atoms are notdirectly bonded to each other.

L¹¹, L¹², and L¹³ are each preferably independently a single bond, —O—,—S—, —CH₂—, —OCH₂—, —CH₂O—, —CO—, —C₂H₄—, —COO—, —OCO—, —OCOOCH₂—,—CH₂OCOO—, —CO—NR^(a)—, —NR^(a)—CO—, —SCH₂—, —CH₂S—, —CH═CH—COO—,—CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CCH₃—COO—, CH═CCH₃—OCO—,—COO—CCH₃═CH—, —OCO—CCH₃═CH—, —COO—CH═CH—COO—, —COO—CH═CH—OCO—,—OCO—CH═CH—COO—, —OCO—CH═CH—OCO—, —COO—CCH₃═CH—COO—, —COO—CCH₃═CH—OCO—,—OCO—CCH₃═CH—COO—, —OCO—CCH₃═CH—OCO—, —COOC₂H₄—, —OCOC₂H₄—, —C₂H₄OCO,—,—C₂H₄COO—, —CH₂COO—, —CH₂OCO—, —COOCH₂—, —OCOCH₂—, —CH═CH—, —CF═CF—,—CF═CH—, —CH═CF—, —CF₂—, —CF₂O—, —OCF₂—, —CF₂CH₂—, —CH₂CF₂—, —CF₂CF₂—,or —C≡C— (where R^(a) represents an alkyl group having 1 to 4 carbonatoms). More preferably, L¹¹, L¹², and L¹³ are each independently asingle bond, —O—, —CH₂—, —OCH₂—, —CH₂O—, —CO—, —C₂H₄—, —COO—, —OCO—,—OCOOCH₂—, —CH₂OCOO—, —CH═CH—COO—, —OCO—CH═CH—, —CH═CCH₃—COO—,—OCO—CCH₃═CH—, —OCO—CH═CH—COO—, —OCO—CCH₃═CH—COO—, —COOC₂H₄—, —OCOC₂H₄—,—C₂H₄OCO—, —C₂H₄COO—, —CH₂COO—, —CH₂OCO—, —COOCH₂—, —OCOCH₂—, or—CH═CH—.

n11 and n12 are each preferably independently 0, 1, or 2. The value ofn11+n12 is 2 or less. When n11 or n12 represents 2, M¹²s or M¹³s, thenumber of which is 2, may be the same or different, and L¹¹s or L¹²s,the number of which is 2, may be the same or different.

When an improvement of the compatibility with other components isparticularly desired, n11+n12 is preferably 0 or 1. When an improvementof the force that controls the alignment of liquid crystal molecules isparticularly desired, n11+n12 is preferably 1 or 2. When thecompatibility with other components is low, for example, deposition ofthe polymerizable compound occurs during the transportation or duringthe production of a liquid crystal display element, which may cause achange in the content of the polymerizable compound or display damage.When the alignment-controlling force is low, for example, the alignmentof liquid crystal molecules changes, which may become a cause of displaydamage.

M¹¹ and M¹⁴ are each preferably independently a 1,4-phenylene group,benzene-1,3,5-triyl group, benzene-1,3,4-triyl group,benzene-1,3,4,5-tetrayl group, 1,4-cyclohexylene group,cyclohexane-1,3,5-triyl group, cyclohexane-1,3,4-triyl group,cyclohexane-1,3,4,5-tetrayl group, pyridine-2,5-diyl group,pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group,naphthalene-2,5,6-triyl group, naphthalene-2,5,6,7-tetrayl group,1,2,3,4-tetrahydronaphthalene-2,6-diyl group,1,2,3,4-tetrahydronaphthalene-2,5,6-triyl group,1,2,3,4-tetrahydronaphthalene-2,5,6,7-tetrayl group, or1,3-dioxane-2,5-diyl group which may be independently unsubstituted orsubstituted with an alkyl group having 1 to 12 carbon atoms, ahalogenated alkyl group having 1 to 12 carbon atoms, an alkoxy grouphaving 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12carbon atoms, a halogen, a cyano group, or a nitro group. Morepreferably, M¹¹ and M¹⁴ are each independently a 1,4-phenylene group,benzene-1,3,5-triyl group, benzene-1,3,4-triyl group,benzene-1,3,4,5-tetrayl group, 1,4-cyclohexylene group,cyclohexane-1,3,5-triyl group, cyclohexane-1,3,4-triyl group,cyclohexane-1,3,4,5-tetrayl group, naphthalene-2,6-diyl group,naphthalene-2,5,6-triyl group, or naphthalene-2,5,6,7-tetrayl groupwhich may be unsubstituted or substituted with an alkyl group having 1to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or ahalogen.

M¹² and M¹³ are each preferably independently a 1,4-phenylene group,1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diylgroup, naphthalene-2,6-diyl group, indane-2,5-diyl group,1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or 1,3-dioxane-2,5-diylgroup which may be unsubstituted or substituted with an alkyl grouphaving 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenatedalkoxy group having 1 to 12 carbon atoms, a halogen, a cyano group, or anitro group. More preferably, M¹¹ and M¹³ are each independently a1,4-phenylene group, 1,4-cyclohexylene group, or naphthalene-2,6-diylgroup which may be unsubstituted or substituted with an alkyl grouphaving 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbonatoms, or a halogen.

In order to improve the compatibility with other components, at leastone of M¹¹ to M¹⁴ is preferably a trans-1,4-Cyclohexylene group, a groupin which at least one hydrogen atom is substituted with a fluorine atom,an alkyl group, or an alkoxy group, or a group in which a spacer groupis not a single bond. In order to improve polymerizability, at least twoof M¹¹ to M¹⁴ are preferably aromatic rings, and three or more of M¹¹ toM¹⁴ are more preferably aromatic rings. When the polymerizability ishigh, the irradiation intensity during polymerization can be reduced,and the amount of residual polymerizable compound is also decreased.Accordingly, the productivity can be improved, degradation of the liquidcrystal composition can be prevented, and image sticking can beprevented. Thus, for example, display damage can be reduced.

Among the structures formed by the combinations of the abovealternatives, —CH═CH—CH═CH—, —C≡C—C≡C—, and —CH═CH—C≡C— are notpreferable from the standpoint of chemical stability. Similarly,structures in which a hydrogen atom in any of these structures issubstituted with a fluorine atom are also not preferable. Similarly,structures in which oxygen atoms are bonded to each other, structures inwhich sulfur atoms are bonded to each other, and structures in which asulfur atom is bonded to an oxygen atom are also not preferable.Similarly, structures in which nitrogen atoms are bonded to each other,structures in which a nitrogen atom is bonded to an oxygen atom, andstructures in which a nitrogen atom is bonded to a sulfur atom are alsonot preferable.

More specifically, the compound represented by general formula (I) ispreferably selected from compounds represented by general formulae (I-1)to (I-153):

wherein p1 and q1 each independently represent an integer of 1 to 12,and p2 and q2 each independently represent an integer of 0 to 12.

Furthermore, the compounds represented by general formulae (I-1) to(I-150) are more preferable.

The polymerizable-compound-containing liquid crystal composition of thepresent invention contains at least one polymerizable compoundrepresented by general formula (I). Thepolymerizable-compound-containing liquid crystal composition of thepresent invention contains preferably one to five, and particularlypreferably one to three polymerizable compounds represented by generalformula (I). When the content of the compound represented by generalformula (I) is small, the force that controls the alignment ofnon-polymerizable liquid crystal compounds is weakened. When the contentof the compound represented by general formula (I) is too large, energynecessary for the polymerization increases, and the amount ofpolymerizable compound that remains without being polymerized increases.Accordingly, the lower limit of the amount of compound represented bygeneral formula (I) is preferably 0.01% by mass, and more preferably0.03% by mass. The upper limit thereof is preferably 2.0% by mass, andmore preferably 1.0% by mass.

In the compound represented by general formula (II), the compound beingused as a second component, R²¹ and R²² are each independentlypreferably an alkyl group having 1 to 10 carbon atoms or an alkenylgroup having 2 to 10 carbon atoms (where one methylene group or two ormore non-adjacent methylene groups in the alkyl group or the alkenylgroup may each be substituted with —O— or —S—, or one or more hydrogenatoms in the alkyl group or the alkenyl group may each be substitutedwith a fluorine atom or a chlorine atom). Among these, an alkyl grouphaving 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms,an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy grouphaving 3 to 6 carbon atoms is more preferable, and an alkyl group having1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms isparticularly preferable.

M²¹, M²², and M²³ are each independently preferably atrans-1,4-cyclohexylene group (where one —CH₂— group or two non-adjacent—CH₂— groups in this trans-1,4-cyclohexylene group may each besubstituted with an oxygen atom), a 1,4-phenylene group (where one —CH═or two or more —CH═ in this 1,4-phenylene group may each be substitutedwith a nitrogen atom), a 3-fluoro-1,4-phenylene group, a3,5-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a1,4-bicyclo[2.2.2]-octylene group, a piperidine-1,4-diyl group, anaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a1,2,3,4-tetrahydronaphthalene-2,6-diyl group. Among these, atrans-1,4-cyclohexylene group, a 1,4-phenylene group, or a1,4-bicyclo[2.2.2]-octylene group is more preferable, and atrans-1,4-cyclohexylene group or a 1,4-phenylene group is particularlypreferable. In the compound represented by general formula (II), o ispreferably 0, 1, or 2, and more preferably 0 or 1. L²¹ and L²² are eachindependently preferably a single bond, —CH₂CH₂—, —(CH₂)₄—, OCH₂—,—CH₂O—, —OCF₂—, —CF₂O—, —CH═CH—, —CH═N—N═CH—, or —C≡C—. Among these, asingle bond, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—, or —CH₂O— is more preferable,and a single bond or —CH₂CH₂— is still more preferable.

Among the structures formed by the combinations of the abovealternatives, —CH═CH—CH═CH—, —C≡C—C≡C—, and —CH═CH—C═—C≡C— are notpreferable from the standpoint of chemical stability. Similarly,structures in which a hydrogen atom in any of these structures issubstituted with a fluorine atom are also not preferable. Similarly,structures in which oxygen atoms are bonded to each other, structures inwhich sulfur atoms are bonded to each other, and structures in which asulfur atom is bonded to an oxygen atom are also not preferable.Similarly, structures in which nitrogen atoms are bonded to each other,structures in which a nitrogen atom is bonded to an oxygen atom, andstructures in which a nitrogen atom is bonded to a sulfur atom are alsonot preferable.

More specifically, the compound represented by general formula (II) ispreferably selected from compounds represented by the group consistingof general formulae (II-A) to (II-P):

wherein R²³ and R²⁴ each independently represent an alkyl group having 1to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, analkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having3 to 10 carbon atoms.

R²³ and R²⁴ are each independently more preferably an alkyl group having1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or analkenyl group having 2 to 10 carbon atoms, and still more preferably analkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 10carbon atoms.

Among the compounds represented by general formulae (II-A) to (II-P),compounds represented by general formulae (II-A), (II-B), (II-C),(II-E), (II-H), (II-I), and (II-K) are preferable, and compoundsrepresented by general formulae (II-A), (II-C), (II-E), (II-H), and(II-I) are more preferable.

The polymerizable-compound-containing liquid crystal composition of thepresent invention contains at least one compound represented by generalformula (II). The polymerizable-compound-containing liquid crystalcomposition of the present invention contains preferably one to ten, andparticularly preferably two to eight compounds represented by generalformula (II). The lower limit of the content of the compound representedby general formula (II) is preferably 5% by mass, more preferably 10% bymass, still more preferably 20% by mass, and particularly preferably 30%by mass. The upper limit of the content of the compound represented bygeneral formula (II) is preferably 80% by mass, more preferably 70% bymass, and still more preferably 60—% by mass.

In the compounds represented by general formulae (IIIa), (IIIb), and(IIIc), the compounds being used as a third component, R³¹, R³², and R³³are each independently preferably a linear alkyl group having 1 to 15carbon atoms or an alkenyl group having 2 to 15 carbon atoms (where onemethylene group or two or more non-adjacent methylene groups in thelinear alkyl group or the alkenyl group may each be substituted with —O—or —S—, and one or more hydrogen atoms in the linear alkyl group or thealkenyl group may each be substituted with a fluorine atom or a chlorineatom), more preferably a linear alkyl group having 1 to 10 carbon atoms,a linear alkoxy group having 1 to 10 carbon atoms, or an alkenyl grouphaving 2 to 10 carbon atoms, and particularly preferably a linear alkylgroup having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbonatoms.

M³¹, M³², M³³, M³⁴, M³⁵, M³⁶, M³⁷, and M³⁸ are each independentlypreferably a trans-1,4-cyclohexylene group (where one methylene group ortwo or more non-adjacent methylene groups in thistrans-1,4-cyclohexylene group may each be substituted with —O— or —S—),a 1,4-phenylene group (where one —CH═ or two or more non-adjacent —CH═in this 1,4-phenylene group may each be substituted with a nitrogenatom), a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]-octylene group,a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or adecahydronaphthalene-2,6-diyl group (where a hydrogen atom contained inany of these groups may be substituted with a cyano group, a fluorineatom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorineatom). Among these, a trans-1,4-cyclohexylene group, a 1,4-phenylenegroup, a 3-fluoro-1,4-phenylene group, or a 3,5-difluoro-1,4-phenylenegroup is more preferable, a trans-1,4-cyclohexylene group or a1,4-phenylene group is still more preferable, and atrans-1,4-cyclohexylene group is particularly preferable.

L³¹, L³², L³³, L³⁴, L³⁵, L³⁶, L³⁷, and L³⁸ are each independentlypreferably a single bond, —OCO—, —COO—, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—,—CH₂O—, —OCF₂—, —CF₂O—, or —C≡C—. Among these, a single bond, —CH₂CH₂—,—(CH₂)₄—, or —C≡C— is more preferable, and a single bond or —CH₂CH₂— isparticularly preferable. X³¹, X³², X³³, X³⁴, X³⁵, X³⁶, and X³⁷ eachindependently represent a hydrogen atom or a fluorine atom. Y³¹, Y³²,and Y³³ each independently represent preferably a hydrogen atom, afluorine atom, a chlorine atom, a cyano group, a thiocyanate group, atrifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethylgroup, a difluoromethoxy group, or an alkyl group having 1 to 12 carbonatoms, more preferably a hydrogen atom, a fluorine atom, a chlorineatom, a cyano group, a trifluoromethoxy group, a trifluoromethyl group,a 2,2,2-trifluoroethyl group, or an alkyl group having 1 to 12 carbonatoms, and particularly preferably a fluorine atom. In the compoundsrepresented by general formulae (IIIa), (IIIb), and (IIIc), p, q, r, s,and t each independently represent 0, 1, or 2, but q+r and s+t eachrepresent 2 or less.

Among the structures formed by the combinations of the abovealternatives, —CH═CH—CH═CH—, —C≡C—C≡C—, and —CH═CH—C≡C— are notpreferable from the standpoint of chemical stability. Similarly,structures in which a hydrogen atom in any of these structures issubstituted with a fluorine atom are also not preferable. Similarly,structures in which oxygen atoms are bonded to each other, structures inwhich sulfur atoms are bonded to each other, and structures in which asulfur atom is bonded to an oxygen atom are also not preferable.Similarly, structures in which nitrogen atoms are bonded to each other,structures in which a nitrogen atom is bonded to an oxygen atom, andstructures in which a nitrogen atom is bonded to a sulfur atom are alsonot preferable.

Specifically, a structure represented by general formula (IIIa-1) belowis preferable.

In general formula (IIIa-1), R³⁴ represents an alkyl group having 1 to 8carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or an alkenylgroup having 2 to 8 carbon atoms, L³⁹ and L⁴⁰ each independentlyrepresent a single bond, —CH₂CH₂—, —(CH₂)₄—, —CH₂—, —CH₂O—, —OCF₂—,—CF₂O—, or —C≡C—, M³⁸ represents a 1,4-phenylene group or atrans-1,4-cyclohexylene group, X³² represents a hydrogen atom or afluorine atom, p₁ represents 0 or 1, and Y³⁴ represents a cyano group, afluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxygroup, a difluoromethoxy group, or a trifluoromethoxy group.

More specifically, structures represented by general formulae (IIIa-2a)to (IIIa-4d) below are preferable.

In general formulae (IIIa-2a) to (IIIa-4d), R³⁴ represents an alkylgroup having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbonatoms, or an alkenyl group having 2 to 8 carbon atoms, X³⁰ and X³² eachindependently represent a hydrogen atom or a fluorine atom, and Y³⁴represents a cyano group, a fluorine atom, a chlorine atom, atrifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group,or a trifluoromethoxy group.

Furthermore, structures represented by general formulae below are alsopreferable.

In the above general formulae, R³⁴ represents an alkyl group having 1 to8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or analkenyl group having 2 to 8 carbon atoms, and Y³⁴ represents a cyanogroup, a fluorine atom, a chlorine atom, a trifluoromethyl group, afluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxygroup.

As for general formula (IIIb), specific structures represented bygeneral formulae below are preferable.

In the above general formulae, R³⁵ represents an alkyl group having 1 to8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or analkenyl group having 2 to 8 carbon atoms, and Y³⁵ represents a cyanogroup, a fluorine atom, a chlorine atom, a trifluoromethyl group, afluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxygroup.

As for general formula (IIIc), specific structures represented bygeneral formulae below are preferable.

In the above general formulae, R³⁶ represents an alkyl group having 1 to8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or analkenyl group having 2 to 8 carbon atoms, and Y³⁶ represents a cyanogroup, a fluorine atom, a chlorine atom, a trifluoromethyl group, afluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxygroup.

The polymerizable-compound-containing liquid crystal composition of thepresent invention may contain at least one compound selected from thegroup consisting of the compounds represented by general formulae(IIIa), (IIIb), and (IIIc). The polymerizable-compound-containing liquidcrystal composition of the present invention contains preferably one toten, and particularly preferably two to eight compounds selected fromthe group consisting of the compounds represented by general formulae(IIIa), (IIIb), and (IIIc). The lower limit of the content of the atleast one compound selected from the group consisting of the compoundsrepresented by general formulae (IIIa), (IIIb), and (IIIc) is preferably5% by mass, more preferably 10% by mass, and particularly preferably 20%by mass. The upper limit of the content thereof is preferably 80% bymass, more preferably 70% by mass, still more preferably 60% by mass,and particularly preferably 50% by mass.

In the compounds represented by general formulae (IVa), (IVb), and(IVc), R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, and R⁴⁶ are each independentlypreferably a linear alkyl group having 1 to 15 carbon atoms or analkenyl group having 2 to 15 carbon atoms (where one methylene group ortwo or more non-adjacent methylene groups in the linear alkyl group orthe alkenyl group may each be substituted with —O— or —S—, and one ormore hydrogen atoms in the linear alkyl group or the alkenyl group mayeach be substituted with a fluorine atom or a chlorine atom), morepreferably a linear alkyl group having 1 to 10 carbon atoms, a linearalkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2to 10 carbon atoms, and particularly preferably a linear alkyl grouphaving 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbonatoms. M⁴¹, M⁴², M⁴³, M⁴⁴, M⁴⁵, M⁴⁶, M⁴⁷, M⁴⁸, and M⁴⁹ are eachindependently preferably a trans-1,4-cyclohexylene group (where onemethylene group or two or more non-adjacent methylene groups in thistrans-1,4-cyclohexylene group may each be substituted with —O— or —S—),a 1,4-phenylene group (where one —CH═ or two or more non-adjacent —CH═in this 1,4-phenylene group may each be substituted with —N═), a1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, apiperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or adecahydronaphthalene-2,6-diyl group (where a hydrogen atom contained inany of these groups maybe substituted with a cyano group, a fluorineatom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorineatom). Among these, a trans-1,4-cyclohexylene group, a 1,4-phenylenegroup, a 3-fluoro-1,4-phenylene group, or a 2,3-difluoro-1,4-phenylenegroup is more preferable, a trans-1,4-cyclohexylene group or a1,4-phenylene group is still more preferable, and atrans-1,4-cyclohexylene group is particularly preferable. L⁴¹, L⁴², L⁴³,L⁴⁴, L⁴⁵, L⁴⁶, L⁴⁷, L⁴⁸, and L⁴⁹ are each independently preferably asingle bond, —CH₂CH₂—, —(CH₂)₄—, —OCO—, —COO—, —OCH₂—, —CH₂O—, —OCF₂—,—CF₂O—, or —C≡C—. Among these, a single bond, —CH₂CH₂—, —OCH₂—, or—CH₂O— is more preferable. X⁴¹, X⁴², X⁴³, X⁴⁴, X⁴⁵, X⁴⁶, X⁴⁷ and X⁴⁸each independently represent a hydrogen atom or a fluorine atom. Grepresents a methylene group or —O—. In the compounds represented bygeneral formulae (IVa), (IVb), and (IVc), u, v, w, x, y, and z eachindependently represent 0, 1, or 2, but u+v, w+x, and y+z each represent2 or less.

Among the structures formed by the combinations of the abovealternatives, —CH═CH—CH═CH—, —C≡C—C≡C—, and —CH═CH—C≡C— are notpreferable from the standpoint of chemical stability. Similarly,structures in which a hydrogen atom in any of these structures issubstituted with a fluorine atom are also not preferable. Similarly,structures in which oxygen atoms are bonded to each other, structures inwhich sulfur atoms are bonded to each other, and structures in which asulfur atom is bonded to an oxygen atom are also not preferable.Similarly, structures in which nitrogen atoms are bonded to each other,structures in which a nitrogen atom is bonded to an oxygen atom, andstructures in which a nitrogen atom is bonded to a sulfur atom are alsonot preferable.

Specifically, the compound represented by general formula (IVa)preferably represents a structure represented by general formula(IVa-1):

wherein R⁴⁷ and R⁴⁸ each independently represent an alkyl group having 1to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or analkenyl group having 2 to 8 carbon atoms, L⁵⁰, L⁵¹, and L⁵² eachindependently represent a single bond, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—,—CH₂O—, —OCF₂—, —CF₂O—, or —C≡C—, M⁵⁰ represents a 1,4-phenylene groupor a trans-1,4-cyclohexylene group, and u₁ and v₁ each independentlyrepresent 0 or 1.

More specifically, structures represented by general formulae (IVa-2a)to (IVa-3i) below are preferable.

In general formulae (IVa-2a) to (IVa-3i), R⁴⁷ and R⁴⁸ each independentlyrepresent an alkyl group having 1 to 8 carbon atoms, an alkoxyl grouphaving 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbonatoms. More preferably, R⁴⁷ and R⁴⁸ each independently represent analkyl group having 1 to 8 carbon atoms or an alkoxyl group having 1 to 8carbon atoms.

Specifically, the compound represented by general formula (IVb)preferably represents a structure represented by general formula(IVb-1):

wherein R⁴⁹ and R⁵⁰ each independently represent an alkyl group having 1to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or analkenyl group having 2 to 8 carbon atoms, L⁵³, L⁵⁴, and L⁵⁵ eachindependently represent a single bond, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—,—CH₂O—, —OCF₂O—, —CF₂O—, or —C≡C—, M⁵¹, M⁵², and M⁵³ each represent a1,4-phenylene group or a trans-1,4-cyclohexylene group, and w1 and x1each independently represent 0, 1, or 2 but w1+x1 represents 2 or less.

More specifically, structures represented by general formulae (IVb-2a)to (IVb-3f) below are preferable.

In general formulae (IVb-2a) to (IVb-3f), R⁴⁹ and R⁵⁰ each independentlyrepresent an alkyl group having 1 to 8 carbon atoms, an alkoxyl grouphaving 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbonatoms.

Specifically, the compound represented by general formula (IVc)preferably represents structures represented by general formulae(IVc-1a) and (IVc-1b):

wherein R⁵¹ and R⁵² each independently represent an alkyl group having 1to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, or analkenyl group having 2 to 8 carbon atoms, L⁵⁶, L⁵⁷, and L⁵⁸ eachindependently represent a single bond, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—,—CH₂O—, —OCF₂—, —CF₂O—, or —C≡C—, M⁵⁴, M⁵⁵, and M⁵⁶ each represent a1,4-phenylene group or a trans-1,4-cyclohexylene group, and y1 and z1each independently represent 0, 1, or 2 but y1+z1 represents 2 or less.

More specifically, structures represented by general formulae (IVc-2a)to (IVc-2g) below are preferable.

In general formulae (IVc-2a) to (IVc-2g), R⁵¹ and R⁵² each independentlyrepresent an alkyl group having 1 to 8 carbon atoms, an alkoxyl grouphaving 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbonatoms.

The polymerizable-compound-containing liquid crystal composition of thepresent invention contains at least one compound selected from the groupconsisting of the compounds represented by general formulae (IIIa),(IIIb), and (IIIc) or at least one compound selected from the groupconsisting of the compounds represented by general formulae (IVa),(IVb), and (IVc), these compounds being used as the third component. Theliquid crystal composition of the present invention contains preferablytwo to ten, and particularly preferably two to eight compounds selectedfrom the group consisting of the compounds represented by generalformulae (IIIa), (IIIb), and (IIIc) or the compounds represented bygeneral formulae (IVa), (IVb), and (IVc). The lower limit of the contentof the at least one compound selected from the group consisting of thecompounds represented by general formulae (IIIa), (IIIb), and (IIIc) orthe compounds represented by general formulae (IVa), (IVb), and (IVc) ispreferably 5% by mass, more preferably 10% by mass, and particularlypreferably 20% by mass. The upper limit of the content thereof ispreferably 80% by mass, more preferably 70% by mass, still morepreferably 60% by mass, and particularly preferably 50% by mass.

In the liquid crystal composition of the present invention, abirefringence Δn is preferably in the range of 0.08 to 0.25.

In the liquid crystal composition of the present invention, a liquidcrystal composition having a positive dielectric anisotropy Δε or anegative dielectric anisotropy Δε can be appropriately selected and useddepending on the display mode of a liquid crystal display element. In aliquid crystal display element of the multi-domain vertical alignment(MVA) mode, a liquid crystal composition having a negative dielectricanisotropy Δε is used. In such a case, the dielectric anisotropy Δε ispreferably −1 or less, and more preferably −2 or less.

The liquid crystal composition of the present invention has a wideliquid crystal phase temperature range (i.e., the absolute value of adifference between the liquid crystal phase lower limit temperature andthe liquid crystal phase upper limit temperature). The liquid crystalphase temperature range is preferably 100° C. or more, and morepreferably 120° C. or more. The liquid crystal phase upper limittemperature is preferably 70° C. or higher, and more preferably 80° C.or higher. Furthermore, the liquid crystal phase lower limit temperatureis preferably −20° C. or lower, and more preferably −30° C. or lower.

The liquid crystal composition of the present invention may contain acommonly used nematic liquid crystal, smectic liquid crystal,cholesteric liquid crystal, or the like besides the compounds describedabove.

According to the polymerizable-compound-containing liquid crystalcomposition of the present invention, polymerization proceeds even inthe absence of a polymerization initiator. However, the liquid crystalcomposition of the present invention may contain a polymerizationinitiator in order to accelerate the polymerization. Examples of thepolymerization initiator include benzoin ethers, benzophenones,acetophenones, benzyl ketals, and acylphosphine oxides.

In order to improve the storage stability of the liquid crystalcomposition of the present invention, a stabilizer may be added to theliquid crystal composition. Examples of the stabilizer that can be usedinclude hydroquinones, hydroquinone monoalkyl ethers, tertiary butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines,β-naphthols, and nitroso compounds. When the stabilizer is used, theamount of stabilizer added is preferably in the range of 0.005% to 1% bymass, more preferably 0.02% to 0.5% by mass, and particularly preferably0.03% to 0.1% by mass relative to the liquid crystal composition.

To the liquid crystal composition of the present invention, a liquidcrystal alignment capability is provided by polymerization of thepolymerizable compound contained in the liquid crystal composition. Theliquid crystal composition of the present invention is used in a liquidcrystal display element in which the amount of transmitted light iscontrolled by using the birefringence of the liquid crystal composition.The liquid crystal composition of the present invention can be usefulfor various liquid crystal display elements, such as an active-matrixliquid crystal display element (AM-LCD), a twisted nematic liquidcrystal display element (TN-LCD), a super twisted nematic liquid crystaldisplay element (STN-LCD), an optically compensated birefringence liquidcrystal display element (OCB-LCD), and an in-plane-switching liquidcrystal display element (IPS-LCD). The liquid crystal composition of thepresent invention is particularly useful for an AM-LCD, and can be usedin a transmissive or reflective liquid crystal display element.

Two substrates of a liquid crystal cell used in a liquid crystal displayelement may be composed of glass or a flexible transparent material suchas a plastic material. One of the substrates may be composed of anopaque material such as silicon. A transparent substrate having atransparent electrode layer can be produced by, for example, sputteringindium tin oxide (ITO) on a transparent substrate such as a glass plate.

A color filter can be produced by, for example, a pigment dispersionmethod, a printing method, an electrodeposition method, or a stainingmethod. A method for producing a color filter will be described bytaking the pigment dispersion method as an example. First, a curablecoloring composition for a color filter is applied onto theabove-mentioned transparent substrate, and is then patterned. Thecurable coloring composition is then cured by heat or light irradiation.These steps are performed for each of three colors of red, green, andblue. Thus, pixel portions for the color filter can be formed.Furthermore, pixel electrodes each including an active element such as athin-film transistor (TFT), a thin-film diode, or ametal-insulator-metal specific resistance element may be provided on thesubstrate.

The substrates are arranged so as to face each other such that thetransparent electrode layer is disposed inside. In this step, the gapbetween the substrates may be adjusted by providing a spacertherebetween. In this case, the gap is preferably adjusted so that thethickness of a light-modulating layer obtained is in the range of 1 to100 μm, and more preferably 1.5 to 10 μm. When a polarizer is used, itis preferable to adjust the product (Δn×d) of the birefringence An ofliquid crystals and a cell thickness d so that the maximum contrast isobtained. When two polarizers are provided, the adjustment may also beperformed so that a satisfactory angle of view and contrast can beobtained by adjusting the polarizing axis of each of the polarizers.Furthermore, a retardation film for widening the angle of view may alsobe used. Examples of the spacer include glass particles, plasticparticles, alumina particles, and photoresist materials. Subsequently, asealant composed of an epoxy thermosetting composition or the like isapplied onto the substrate by screen printing so as to form aliquid-crystal injection port. The substrates are then bonded to eachother, and the sealant is thermally cured by heating.

As a method for interposing the liquid crystal composition between thetwo substrates, a commonly used vacuum injection method, a one-drop-fill(ODF) method, or the like can be employed.

As a method for polymerizing the polymerizable compound, a method inwhich polymerization is conducted by applying an active energy ray suchas ultraviolet light or an electron beam is preferable because rapidprogress of polymerization is desirable. In the case where ultravioletlight is used, either a polarized light source or an unpolarized lightsource may be used. When polymerization is conducted in a state in whichthe liquid crystal composition is interposed between two substrates, itis necessary that at least a substrate disposed on the irradiationsurface side have transparency appropriate for the active energy ray.Also, only specific portions may be polymerized using a mask duringlight irradiation, and unpolymerized potions may then be polymerized byfurther applying an active energy ray while changing the alignment stateof the unpolymerized potions by changing a condition such as theelectric field, the magnetic field, or the temperature. In particular,when ultraviolet exposure is performed, the ultraviolet exposure ispreferably performed while applying an AC electric field to thepolymerizable-compound-containing liquid crystal composition. As for theAC electric field applied, a frequency of 10 Hz to 10 kHz is preferable,a frequency of 60 Hz to 10 kHz is more preferable, and the voltage isselected in accordance with a desired pretilt angle of the liquidcrystal display element. That is, the pretilt angle of the liquidcrystal display element can be controlled by the voltage applied. In aliquid crystal display element of the MVA mode, it is preferable tocontrol the pretilt angle to 80 to 89 degrees from the standpoint ofalignment stability and the contrast.

The temperature during the irradiation is preferably within atemperature range in which the liquid crystal state of the liquidcrystal composition of the present invention is maintained.Polymerization is preferably conducted at a temperature close to roomtemperature, that is, typically at a temperature in the range of 15° C.to 35° C. A metal halide lamp, a high-pressure mercury lamp, anultrahigh-pressure mercury lamp, or the like can be used as a lamp forgenerating ultraviolet light. As for the wavelength of ultraviolet lightradiated, it is preferable to radiate ultraviolet light in a wavelengthrange which is not included in an absorption wavelength range of theliquid crystal composition. Preferably, a certain wavelength range ofultraviolet light is cut off and used, as required. The intensity ofultraviolet light irradiated is preferably 0.1 mW/cm² to 100 W/cm², andmore preferably 2 mW/cm² to 50 W/cm². The amount of energy of theultraviolet light irradiated can be appropriately adjusted, but ispreferably 10 mJ/cm² to 500 J/cm², and more preferably 100 mJ/cm² to 200J/cm². During the irradiation of ultraviolet light, the intensity of theultraviolet light may be changed. The ultraviolet-irradiation time isappropriately selected in accordance with the intensity of theultraviolet light irradiated, but is preferably 10 to 3,600 seconds.

EXAMPLES

The present invention will be described in more detail byway ofExamples, but the present invention is not limited to these Examples. Itshould be noted that “%” in compositions of Examples and ComparativeExample described below represents “% by mass” unless otherwise stated.

Physical properties of liquid crystal compositions are represented asfollows:

-   T_(N-I) (° C.): Nematic phase-isotropic liquid phase transition    temperature (liquid crystal phase upper limit temperature)-   Δε: Dielectric anisotropy-   Δn: Birefringence-   V_(th) (V): An applied voltage with which the transmittance is    changed by 10% when a square wave with a frequency of 1 kHz is    applied (threshold voltage)

Method for Measuring Amount of Residual Monomer After UV Curing

A liquid crystal composition was injected into a liquid crystal cell,and the cell was then irradiated with ultraviolet (UV) light topolymerize a polymerizable compound. Subsequently, the liquid crystalcell was disassembled, and an acetonitrile solution of an elutioncomponent containing liquid crystal materials, a polymerized product,and an unpolymerized polymerizable compound was prepared. This solutionwas analyzed by high-performance liquid chromatography (column:reversed-phase nonpolar column, developing solvent: acetonitrile) tomeasure the peak area of each component. The amount of residualpolymerizable compound was determined from the ratio of the peak area ofthe unpolymerized polymerizable compound to the peak area of a liquidcrystal material used as an indicator. The amount of residual monomerwas determined from this value and the amount of polymerizable compoundinitially added. The detection limit of the amount of residualpolymerizable compound was 1,000 ppm.

Example 1

A liquid crystal composition LC-1 containing at least one compoundselected from the compounds represented by general formula (II) and atleast one compound selected from the compounds represented by generalformulae (IIIa), (IIIb), and (IIIc) or at least one compound selectedfrom the compounds represented by general formulae (IVa), (IVb), and(IVc) was prepared. The compounds constituting the liquid crystalcomposition LC-1 and the proportions of the compounds are as follows.

Table 1 shows the physical properties of the liquid crystal compositionLC-1.

TABLE 1 T_(N−I) (° C.) 80 Δε −3.5 Δn 0.087

A polymerizable-compound-containing liquid crystal composition CLC-1 wasprepared by adding 0.3% of a polymerizable compound represented byformula (I-40-a) below to 99.7% of the liquid crystal composition LC-1and uniformly dissolving the polymerizable compound.

The physical properties of the polymerizable-compound-containing liquidcrystal composition CLC-1 were substantially the same as those of theliquid crystal composition LC-1. Thus, it was found that thepolymerizable compound represented by formula (I-40-a) did not degradethe liquid crystal properties of the liquid crystal composition addedthereto. This polymerizable-compound-containing liquid crystalcomposition CLC-1 was stored in a cold place (at −20° C.) for one week.Consequently, deposition or the like did not occur. Thus, it was foundthat the polymerizable compound represented by formula (I-40-a) had agood compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-1was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured (by a crystal rotation method),and the liquid crystal cell was then irradiated with ultraviolet lightusing a high-pressure mercury lamp through a filter that cuts offultraviolet light of 320 nm or less while applying a square wave of 1.8V at a frequency of 1 kHz. The irradiation intensity on the surface ofthe cell was adjusted to 15 mW/cm², and the irradiation was performedfor 600 seconds, thus obtaining a homeotropic-alignment liquid crystaldisplay element in which the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-1 waspolymerized. Table 2 shows the pretilt angles of the element measuredbefore and after the ultraviolet irradiation and an electro-opticproperty of the element.

TABLE 2 Pretilt angle before 89.6 ultraviolet irradiation (°) Pretiltangle after 86.7 ultraviolet irradiation (°) V_(th) (V) 1.65

The above results of the pretilt angles show that analignment-controlling force acting on the liquid crystal composition wasgenerated by polymerization of the polymerizable compound, and ahomeotropic-alignment liquid crystal display element was obtained inwhich the pretilt angle was fixed in a state where liquid crystalmolecules were tilted at 2.9 degrees with respect to the initial state.

Furthermore, the content of the unpolymerized polymerizable compoundrepresented by formula (I-40-a) in the element was analyzed by liquidchromatography, but the unpolymerized polymerizable compound was notdetected. Thus, it was confirmed that the polymerizable compoundrepresented by formula (I-40-a) could be polymerized without using apolymerization initiator, and that the content of the unpolymerizedproduct remaining after the polymerization was equal to or less than thedetection limit.

Comparative Example 1

A polymerizable-compound-containing liquid crystal composition CLC-A wasprepared by adding 0.3% of a polymerizable compound represented byformula (A) to 99.7% of the liquid crystal composition LC-1 anduniformly dissolving the polymerizable compound.

The polymerizable-compound-containing liquid crystal composition CLC-Awas injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-A waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 87.4 degrees whereas the pretilt angle before theultraviolet irradiation was 89.6 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state.However, according to the analytical result of the content of theunpolymerized polymerizable compound represented by formula (A) in theelement, the result being obtained by liquid chromatography, the contentof the unpolymerized polymerizable compound was 1,200 ppm. Thus, thepolymerization of the polymerizable compound (A) did not completelyproceed. In addition, this polymerizable-compound-containing liquidcrystal composition CLC-A was stored in a cold place (at −20° C.) forone week. Consequently, deposition occurred. Thus, it was found thatthis polymerizable compound represented by formula (A) had a poorcompatibility with other liquid crystal compounds.

Example 2

A polymerizable-compound-containing liquid crystal composition CLC-2 wasprepared by adding 0.5% of the polymerizable compound represented byformula (I-40-a) to 99.5% of the liquid crystal composition LC-1 anduniformly dissolving the polymerizable compound. It was found that thepolymerizable compound represented by formula (I-40-a) did not degradethe liquid crystal properties of the liquid crystal composition added,as in Example 1. This polymerizable-compound-containing liquid crystalcomposition CLC-2 was stored in a cold place (at −20° C.) for one week.Consequently, deposition or the like did not occur. Thus, it was foundthat the polymerizable compound represented by formula (I-40-a) had agood compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-2was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-2 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 86.2 degrees whereas the pretilt angle before theultraviolet irradiation was 89.7 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (I-40-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (I-40-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 3

A polymerizable-compound-containing liquid crystal composition CLC-3 wasprepared by adding 0.3% of a polymerizable compound represented byformula (I-42-a) to 99.7% of the liquid crystal composition LC-1 anduniformly dissolving the polymerizable compound.

It was found that the polymerizable compound represented by formula(I-42-a) did not degrade the liquid crystal properties, and had a goodcompatibility as in the polymerizable compound represented by formula(I-40-a) and used in Example 1. This polymerizable-compound-containingliquid crystal composition CLC-3 was stored in a cold place (at −20⁰C)for one week. Consequently, deposition or the like did not occur. Thus,it was found that the polymerizable compound represented by formula(I-42-a) had a good compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-3was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-3 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 86.6 degrees whereas the pretilt angle before theultraviolet irradiation was 89.6 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (I-42-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (I-42-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 4

A polymerizable-compound-containing liquid crystal composition CLC-4 wasprepared by adding 0.3% of a polymerizable compound represented byformula (I-5-a) to 99.7% of the liquid crystal composition LC-1 anduniformly dissolving the polymerizable compound.

It was found that the polymerizable compound represented by formula(I-5-a) did not degrade the liquid crystal properties, and had a goodcompatibility as in the compound represented by formula (I-40-a) andused in Example 1. This polymerizable-compound-containing liquid crystalcomposition CLC-4 was stored in a cold place (at −20° C.) for one week.Consequently, deposition or the like did not occur. Thus, it was foundthat the polymerizable compound represented by formula (I-5-a) had agood compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-4was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-4 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 86.7 degrees whereas the pretilt angle before theultraviolet irradiation was 89.8 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (I-5-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (I-5-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 5

A polymerizable-compound-containing liquid crystal composition CLC-5 wasprepared by adding 0.3% of the polymerizable compound represented byformula (I-20-a) to 99.7% of the liquid crystal composition LC-1 anduniformly dissolving the polymerizable compound.

It was found that the polymerizable compound represented by formula(I-20-a) did not degrade the liquid crystal properties, and had a goodcompatibility as in the polymerizable compound represented by formula(I-40-a) and used in Example 1. This polymerizable-compound-containingliquid crystal composition CLC-5 was stored in a cold place (at −20° C.)for one week. Consequently, deposition or the like did not occur. Thus,it was found that the polymerizable compound represented by formula(I-20-a) had a good compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-5was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-5 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 87.2 degrees whereas the pretilt angle before theultraviolet irradiation was 89.6 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (I-20-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (I-20-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 6

A polymerizable-compound-containing liquid crystal composition CLC-6 wasprepared by adding 0.3% of the polymerizable compound represented byformula (I-66-a) to 99.7% of the liquid crystal composition LC-1 anduniformly dissolving the polymerizable compound.

It was found that the polymerizable compound represented by formula(I-66-a) did not degrade the liquid crystal properties, and had a goodcompatibility as in the polymerizable compound represented by formula(I-40-a) and used in Example 1. This polymerizable-compound-containingliquid crystal composition CLC-6 was stored in a cold place (at −20° C.)for one week. Consequently, deposition or the like did not occur. Thus,it was found that the polymerizable compound represented by formula(I-66-a) had a good compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-6was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-6 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 86.3 degrees whereas the pretilt angle before theultraviolet irradiation was 89.7 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (I-66-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (I-66-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 7

A polymerizable-compound-containing liquid crystal composition CLC-7 wasprepared by adding 0.3% of the polymerizable compound represented byformula (I-144-a) to 99.7% of the liquid crystal composition LC-1 anduniformly dissolving the polymerizable compound.

It was found that the polymerizable compound represented by formula(I-144-a) did not degrade the liquid crystal properties, and had a goodcompatibility as in the polymerizable compound represented by formula(I-40-a) and used in Example 1. This polymerizable-compound-containingliquid crystal composition CLC-7 was stored in a cold place (at −20° C.)for one week. Consequently, deposition or the like did not occur. Thus,it was found that the polymerizable compound represented by formula(I-144-a) had a good compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-7was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-7 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 86.2 degrees whereas the pretilt angle before theultraviolet irradiation was 89.8 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (1-144-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (1-144-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 8

A liquid crystal composition LC-2 containing the components below wasprepared as a sample containing at least one compound selected from thecompounds represented by general formula (II) and at least one compoundselected from the compounds represented by general formulae (IIIa),(IIIb), and (IIIc) or at least one compound selected from the compoundsrepresented by general formulae (IVa), (IVb), and (IVc).

Table 3 shows the physical properties of the liquid crystal compositionLC-2.

TABLE 3 T_(N−I) (° C.) 85 Δε −3.4 Δn 0.094

A polymerizable-compound-containing liquid crystal composition CLC-8 wasprepared by adding 0.3% of the polymerizable compound represented byformula (I-40-a) to 99.7% of the liquid crystal composition LC-2 anduniformly dissolving the polymerizable compound. It was found that thepolymerizable compound represented by formula (I-40-a) did not degradethe liquid crystal properties, and had a good compatibility as inExample 1. This polymerizable-compound-containing liquid crystalcomposition CLC-8 was stored in a cold place (at −20° C.) for one week.Consequently, deposition or the like did not occur. Thus, it was foundthat the polymerizable compound represented by formula (I-40-a) had agood compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-8was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-8 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 86.6 degrees whereas the pretilt angle before theultraviolet irradiation was 89.8 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the in initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (I-40-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (I-40-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 9

A liquid crystal composition LC-3 containing the components below wasprepared as a sample containing at least one compound selected from thecompounds represented by general formula (II) and at least one compoundselected from the compounds represented by general formulae (IIIa),(IIIb), and (IIIc) or at least one compound selected from the compoundsrepresented by general formulae (IVa), (IVb), and (IVc).

Table 4 shows the physical properties of the liquid crystal compositionLC-3.

TABLE 4 T_(N−I) (° C.) 72 Δε −3.3 Δn 0.086

A polymerizable-compound-containing liquid crystal composition CLC-9 wasprepared by adding 0.3% of the polymerizable compound represented byformula (I-40-a) to 99.7% of the liquid crystal composition LC-3 anduniformly dissolving the polymerizable compound. It was found that thepolymerizable compound represented by formula (I-40-a) did not degradethe liquid crystal properties, and had a good compatibility as inExample 1. This polymerizable-compound-containing liquid crystalcomposition CLC-9 was stored in a cold place (at −20° C.) for one week.Consequently, deposition or the like did not occur. Thus, it was foundthat the polymerizable compound represented by formula (I-40-a) had agood compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-9was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homeotropic alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homeotropic-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-9 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 87.0 degrees whereas the pretilt angle before theultraviolet irradiation was 89.7 degrees. Thus, the pretilt angle of theliquid crystal molecules was fixed in a state in which the liquidcrystal molecules were tilted with respect to the initial state. Thecontent of the unpolymerized polymerizable compound represented byformula (I-40-a) in the element was analyzed by liquid chromatography.The content of the unpolymerized polymerizable compound was equal to orless than the detection limit. Thus, it was confirmed that thepolymerizable compound represented by formula (I-40-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Example 10

A liquid crystal composition LC-4 containing the components below wasprepared as a sample containing at least one compound selected from thecompounds represented by general formula (II) and at least one compoundselected from the compounds represented by general formulae (IIIa),(IIIb), and (IIIc) or at least one compound selected from the compoundsrepresented by general formulae (IVa), (IVb), and (IVc).

Table 5 shows the physical properties of the liquid crystal compositionLC-4.

TABLE 5 T_(N−I) (° C.) 85 Δε 5.5 Δn 0.090

A polymerizable-compound-containing liquid crystal composition CLC-10was prepared by adding 0.3% of the polymerizable compound represented byformula (I-40-a) to 99.7% of the liquid crystal composition LC-4 anduniformly dissolving the polymerizable compound. It was found that thepolymerizable compound represented by formula (I-40-a) did not degradethe liquid crystal properties, and had a good compatibility as inExample 1. This polymerizable-compound-containing liquid crystalcomposition CLC-10 was stored in a cold place (at −20° C.) for one week.Consequently, deposition or the like did not occur. Thus, it was foundthat the polymerizable compound represented by formula (I-40-a) had agood compatibility with other liquid crystal compounds.

The polymerizable-compound-containing liquid crystal composition CLC-10was injected, by a vacuum injection method, into a cell having an ITOelectrode layer, the cell having a cell gap of 3.5 μm and includingpolyimide alignment layers that induce a homogeneous alignment. Thepretilt angle of this cell was measured, and the liquid crystal cell wasthen irradiated with ultraviolet light using a high-pressure mercurylamp through a filter that cuts off ultraviolet light of 320 nm or lesswhile applying a square wave of 1.8 V at a frequency of 1 kHz. Theirradiation intensity on the surface of the cell was adjusted to 15mW/cm², and the irradiation was performed for 600 seconds, thusobtaining a homogeneous-alignment liquid crystal display element inwhich the polymerizable compound in thepolymerizable-compound-containing liquid crystal composition CLC-10 waspolymerized. The pretilt angle after the ultraviolet irradiation of theelement was 3.6 degrees whereas the pretilt angle before the ultravioletirradiation was 0.3 degrees. Thus, a pretilt angle was provided, and thepretilt angle of the liquid crystal molecules was fixed in a state inwhich the liquid crystal molecules were tilted with respect to theinitial state. The content of the unpolymerized polymerizable compoundrepresented by formula (I-40-a) in the element was analyzed by liquidchromatography. The content of the unpolymerized polymerizable compoundwas equal to or less than the detection limit. Thus, it was confirmedthat the polymerizable compound represented by formula (I-40-a) could bepolymerized without using a polymerization initiator, and that thecontent of the unpolymerized product remaining after the polymerizationwas equal to or less than the detection limit.

Evaluation

A voltage was applied to the liquid crystal display elements afterpolymerization, the liquid crystal display elements being prepared inExamples 1 to 10 and Comparative Example 1, and the state of imagesticking was visually observed with elapsed time. Table 6 shows theresults. In Table 6, symbol A represents that no change was observed.Symbol B represents that image sticking was observed, and a largernumber of symbol B's represents that the image sticking was more severe.

TABLE 6 After 10 After 50 After 100 After 500 hours hours hours hoursExample 1 A A A A Example 2 Example 3 Example 4 Example 5 Example 6Example 7 Example 8 Example 9 Example 10 Comparative B BB BBB Example 1

In the liquid crystal display element prepared in Comparative Example 1,image sticking occurred after 48 hours from the start of display, anddisplay damage was observed over the substantially entire surface after168 hours. In contrast, in the liquid crystal display elements preparedin Examples 1 to 10, a satisfactory display state was maintained evenafter 500 hours had passed. According to these results, it was possibleto confirm the high reliability of liquid crystal display elements inwhich all polymerizable materials were polymerized and consumed, as inthe compounds of the present invention. Furthermore, it was found that adecrease in the alignment-controlling force did not occur, and thus thepolymers had a sufficiently high rigidity.

1. A polymerizable-compound-containing liquid crystal compositioncomprising: as a first component, at least one polymerizable compoundrepresented by general formula (I):(Z¹¹)_(m11)-M¹¹-(L¹¹-M¹²)_(n11)-COO-(M¹³-L¹²)_(n12)-M¹⁴(Z¹²)_(m12)   (I)(wherein Z¹¹ and Z¹² each independently represent a hydrogen atom, afluorine atom, a chlorine atom, a cyano group, a thiocyanate group, atrifluoromethoxy group, a trifluoromethyl group, a difluoromethoxygroup, or an alkyl group having 1 to 12 carbon atoms where a methylenegroup in the alkyl group may be substituted with an oxygen atom, asulfur atom, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, or —C≡C— as long asoxygen atoms are not directly bonded to each other, or Z¹¹ and Z¹² eachindependently represent -L¹³-S¹¹—R¹¹ (where L¹³s each independentlyrepresent a single bond, —O—, —S—, —CH₂—, —OCH₂—, —CH₂O—, —CO—, —C₂H₄—,—COO—, —OCO—, —OCOOCH₂—, —CH₂OCOO—, —CO—NR^(a)—, —NR^(a)—CO—, —SCH₂—,—CH₂S—, —CH═CR^(a)—COO—, —CH═CR^(a)—OCO—, —COO—CR^(a)═CH—,—OCO—CR^(a)═CH—, —COO—CR^(a)═CH—COO—, —COO—CR^(a)═CH—OCO—,—OCO—CR^(a)═CH—COO—, —OCO—CR^(a)═CH—OCO—, —COOC₂H₄—, —OCOC₂H₄—,—C₂H₄OCO—, —C₂H₄COO—, —CH₂COO—, —CH₂OCO—, —COOCH₂—, —OCOCH₂—, —CH═CH—,—CF═CF—, —CF═CH—, —CH═CF—, —CF₂—, —CF₂O—, —OCF₂—, —CF₂CH₂—, —CH₂CF₂—,—CF₂CF₂—, or —C≡C— (where R^(a)s each independently represent a hydrogenatom or an alkyl group having 1 to 4 carbon atoms), S¹¹s eachindependently represent an alkylene group having 1 to 12 carbon atoms ora single bond, where a methylene group in the alkylene group may besubstituted with —O—, —COO—, —OCO—, or —OCOO— as long as oxygen atomsare not directly bonded to each other, R¹¹s each independently representany one of formulae (R-1) to (R-15):

however, at least one of Z¹¹ and Z¹² represents -L¹³-S¹¹—R¹¹, M¹¹ andM¹⁴ each independently represent a 1,4-phenylene group, abenzene-1,3,5-triyl group, a benzene-1,3,4-triyl group, abenzene-1,3,4,5-tetrayl group, a 1,4-cyclohexylene group, acyclohexane-1,3,5-triyl group, a cyclohexane-1,3,4-triyl group, acyclohexane-1,3,4,5-tetrayl group, a pyridine-2,5-diyl group, apyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, anaphthalene-2,5,6-triyl group, a naphthalene-2,5,6,7-tetrayl group, a1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a1,2,3,4-tetrahydronaphthalene-2,5,6-triyl group, a1,2,3,4-tetrahydronaphthalene-2,5,6,7-tetrayl group, or a1,3-dioxane-2,5-diyl group, M¹¹ and M¹⁴ may each be independentlyunsubstituted or substituted with an alkyl group having 1 to 12 carbonatoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxygroup having 1 to 12 carbon atoms, a halogenated alkoxy group having 1to 12 carbon atoms, a halogen, a cyano group, or a nitro group, L¹¹ andL¹² each independently represent the same group as that represented byL¹³, M¹² and M¹³ each independently represent a 1,4-phenylene group, a1,4-cyclohexylene group, a pyridine-2,5-diyl group, apyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, anindane-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group,or a 1,3-dioxane-2,5-diyl group, M¹² and M¹³ may each be independentlyunsubstituted or substituted with an alkyl group having 1 to 12 carbonatoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxygroup having 1 to 12 carbon atoms, a halogenated alkoxy group having 1to 12 carbon atoms, a halogen, a cyano group, or a nitro group, m11 andm12 each independently represent 1, 2, or 3, and when m11 and/or m12represents 2 or 3, Z¹¹s and/or Z¹²s, the number of which is 2 or 3, maybe the same or different, and n11 and n12 each independently represent0, 1, or 2, but n11+n12 is 2 or less, and when n11 or n12 represents 2,M¹²s or M¹³s, the number of which is 2, may be the same or different andL¹¹s or L¹²s, the number of which is 2, maybe the same or different); asa second component, at least one compound represented by general formula(II):R²¹-M²¹-L²¹-M²²-(L²²-M²³)_(o)-R²²   (II) (wherein R²¹ and R²² eachindependently represent an alkyl group having 1 to 10 carbon atoms or analkenyl group having 2 to 10 carbon atoms, one methylene group or two ormore non-adjacent methylene groups in the alkyl group or the alkenylgroup may each be substituted with —O— or —S—, and one or more hydrogenatoms in the alkyl group or the alkenyl group may each be substitutedwith a fluorine atom or a chlorine atom, M²¹, M²², and M²³ eachindependently represent a group selected from the groups consisting of(a) a trans-1,4-cyclohexylene group (where one methylene group or two ormore non-adjacent methylene groups in the trans-1,4-cyclohexylene groupmay each be substituted with —O— or —S—), (b) a 1,4-phenylene group(where one —CH═ or two or more non-adjacent —CH═ in the 1,4-phenylenegroup may each be substituted with a nitrogen atom), a2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, and a3,5-difluoro-1,4-phenylene group, and (c) a 1,4-cyclohexenylene group, a1,4-bicyclo[2.2.2]octylene group, a piperidine-2,5-diyl group, anaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, and a1,2,3,4-tetrahydronaphthalene-2,6-diyl group, o represents 0, 1, or 2,L²¹ and L²² each independently represent a single bond, —CH₂CH₂—,—(CH₂)₄—, —OCH₂—, —CH₂O—, —OCF₂—, —CF₂O—, —CH═CH—, —CH═N—N═CH—, or—C≡C—, when a plurality of L²²s are present, L²²s may be the same ordifferent, and when a plurality of M²³s are present, M²³s may be thesame or different); and as a third component, at least one compoundselected from the group consisting of compounds represented by generalformulae (IIIa), (IIIb), and (IIIc):

(wherein R³¹, R³², and R³³ each independently represent an alkyl grouphaving 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbonatoms, one methylene group or two or more non-adjacent methylene groupsin the alkyl group or the alkenyl group may each be substituted with —O—or —S—, and one or more hydrogen atoms in the alkyl group or the alkenylgroup may each be substituted with a fluorine atom or a chlorine atom,M³¹, M³², M³³, M³⁴, M³⁵, M³⁶, M³⁷, and M³⁸; each independently representa group selected from the groups consisting of (d) atrans-1,4-cyclohexylene group (where one methylene group or two or morenon-adjacent methylene groups in the trans-1,4-cyclohexylene group mayeach be substituted with —O— or —S—), (e) a 1,4-phenylene group (whereone —CH═ or two or more non-adjacent —CH═ in the 1,4-phenylene group mayeach be substituted with —N═), a 3-fluoro-1,4-phenylene group, and a3,5-difluoro-1,4-phenylene group, and (f) a 1,4-cyclohexenylene group, a1,4-bicyclo[2.2.2]octylene group, a piperidine-2,5-diyl group, anaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diylgroup, and a decahydronaphthalene-2,6-diyl group, a hydrogen atomcontained in any of the groups (d), (e), and (f) may be substituted witha cyano group, a fluorine atom, a trifluoromethyl group, atrifluoromethoxy group, or a chlorine atom, L³¹, L³², L³³, L³⁴, L³⁵,L³⁶, L³⁷, and L³⁸ each independently represent a single bond, —COO—,—OCO—, —CH₂CH₂—, —(CH₂)₄—, —OCH₂—, —CH₂O—, —OCF₂—, —CF₂O—, or —C≡C—,when a plurality of M³²s, M³⁴s, M³⁵s, M³⁷s, M³⁸s, L³¹s, L³³s, L³⁵s,L³⁶s, and/or L³⁸s are present, they may be the same or different, X³¹,X³², X³³, X³⁴, X³⁵, X³⁶, and X³⁷ each independently represent a hydrogenatom or a fluorine atom, Y³¹, Y³², and Y³³ each independently representa fluorine atom, a chlorine atom, a cyano group, a thiocyanate group, atrifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethylgroup, or a difluoromethoxy group, and p, q, r, s, and t eachindependently represent 0, 1, or 2, but q+r and s+t are each 2 or less),or at least one compound selected from the group consisting of compoundsrepresented by general formulae (IVa), (IVb), and (IVc):

(wherein R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, and R⁴⁶ each independently representan alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2to 10 carbon atoms, one methylene group or two or more non-adjacentmethylene groups in the alkyl group or the alkenyl group may each besubstituted with —O— or —S—, and one or more hydrogen atoms in the alkylgroup or the alkenyl group may each be substituted with a fluorine atomor a chlorine atom, M⁴¹, M⁴², M⁴³, M⁴⁴, M⁴⁵, M⁴⁶, M⁴⁷, M⁴⁸, and M⁴⁹ eachindependently represent a group selected from the groups consisting of(g) a trans-1,4-cyclohexylene group (where one methylene group or two ormore non-adjacent methylene groups in the trans-1,4-cyclohexylene groupmay each be substituted with —O— or —S—), (h) a 1,4-phenylene group(where one —CH═ or two or more non-adjacent —CH═ in the 1,4-phenylenegroup may each be substituted with a nitrogen atom), and (i) a1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, apiperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and adecahydronaphthalene-2,6-diyl group, a hydrogen atom contained in any ofthe groups (g), (h), and (i) may be substituted with a cyano group, afluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or achlorine atom, L⁴¹, L⁴², L⁴³, L⁴⁴, L⁴⁵, L⁴⁶, L⁴⁷, L⁴⁸, and L⁴⁹ eachindependently represent a single bond, —COO—, —OCO—, —CH₂CH₂—, —(CH₂)₄—,—OCH₂—, —CH₂O—, —OCF₂—, —CF₂O—, or —C≡C—, when a plurality of M⁴²s,M⁴³s, M⁴⁵s, M⁴⁶s, M⁴⁸s, M⁴⁹s, L⁴¹s, L⁴³s, L⁴⁴s, L⁴⁶s, L⁴⁷s and/or L⁴⁹sare present, they may be the same or different, X⁴¹, X⁴², X⁴³, X⁴⁴, X⁴⁵,X⁴⁶, X⁴⁷ and X⁴⁸ each independently represent a hydrogen atom, atrifluoromethyl group, a trifluoromethoxy group, or a fluorine atom,however, at least one of X⁴¹ and X⁴² represents a fluorine atom, atleast one of X⁴³, X⁴⁴, and X⁴⁵ represents a fluorine atom, at least oneof X⁴⁶, X⁴⁷, and X⁴⁸ represents a fluorine atom, X⁴⁶ and X⁴⁷ do notrepresent fluorine atoms at the same time, and X⁴⁶ and X⁴⁸ do notrepresent fluorine atoms at the same time, G represents a methylenegroup or —O—, and u, v, w, x, y, and z each independently represent 0,1, or 2, but u+v, w+x, and y+z are each 2 or less).
 2. Thepolymerizable-compound-containing liquid crystal composition accordingto claim 1, wherein, in general formula (I), Z¹¹ and Z¹² each represent-L¹³-S¹¹—R¹¹, and at least one of S¹¹s represents an alkylene grouphaving 2 to 12 carbon atoms where a methylene group in the alkylenegroup may be substituted with —O—, —COO—, —OCO—, or —OCOO— as long asoxygen atoms are not directly bonded to each other.
 3. Thepolymerizable-compound-containing liquid crystal composition accordingto claim 1, wherein, in general formula (I), at least two of Z¹¹s andZ¹²s are each -L¹³-S¹¹—R¹¹.
 4. The polymerizable-compound-containingliquid crystal composition according to claim 1, wherein, in generalformula (I), R¹¹s each independently represent formula (R-1) or (R-2).5. The polymerizable-compound-containing liquid crystal compositionaccording to claim 1, wherein, in general formula (I), the sum of n11and n12 is 0 or
 1. 6. The polymerizable-compound-containing liquidcrystal composition according to claim 1, wherein, in general formula(I), M¹¹ and M¹⁴ each independently represent a 1,4-phenylene group,benzene-1,3,5-triyl group, benzene-1,3,4-triyl group,benzene-1,3,4,5-tetrayl group, naphthalene-2,6-diyl group,naphthalene-2,5,6-triyl group, or naphthalene-2,5,6,7-tetrayl groupwhich may be unsubstituted or substituted with an alkyl group having 1to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbonatoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxygroup having 1 to 12 carbon atoms, a halogen, a cyano group, or a nitrogroup.
 7. The polymerizable-compound-containing liquid crystalcomposition according to claim 1, wherein, in general formula (I), M¹²and M¹³ each independently represent a 1,4-phenylene group ornaphthalene-2,6-diyl group which may be unsubstituted or substitutedwith an alkyl group having 1 to 12 carbon atoms, a halogenated alkylgroup having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbonatoms, a halogenated alkoxy group having 1 to 12 carbon atoms, ahalogen, a cyano group, or a nitro group.
 8. Thepolymerizable-compound-containing liquid crystal composition accordingto claim 1, wherein the liquid crystal composition is used in a liquidcrystal display element including a pair of substrates, a liquid crystalinterposed between the substrates, a transparent electrode, and apolarizer, in which a liquid crystal alignment capability is provided bypolymerizing a polymerizable compound contained in the liquid crystalcomposition.
 9. The polymerizable-compound-containing liquid crystalcomposition according to claim 1, wherein the liquid crystal compositioncontains 0.01% to 2% by mass of the at least one compound selected fromthe polymerizable compounds represented by general formula (I), 5% to70% by mass of the at least one compound selected from the compoundsrepresented by general formula (II), and 5% to 70% by mass of the atleast one compound selected from the group consisting of the compoundsrepresented by general formulae (IIIa), (IIIb), and (IIIc) or thecompounds represented by general formulae (IVa), (IVb), and (IVc). 10.The polymerizable-compound-containing liquid crystal compositionaccording to claim 1, wherein the liquid crystal composition contains,as the third component, at least one compound selected from the groupconsisting of the compounds represented by general formulae (IVa),(IVb), and (IVc).
 11. A liquid crystal display element comprising: thepolymerizable-compound-containing liquid crystal composition accordingto claim 1, wherein a liquid crystal alignment capability is provided bypolymerizing the at least one polymerizable compound contained in thepolymerizable-compound-containing liquid crystal composition.
 12. Theliquid crystal display element according to claim 11, wherein adielectric anisotropy of the polymerizable-compound-containing liquidcrystal composition is negative.